Hydroxylation of 1,8-cineole by Mucor ramannianusand Aspergillus niger

• Autor(a) principal: Ramos,Aline de Souza
• Data de Publicação: 2015
• Outros Autores: Ribeiro,Joyce Benzaquem, Teixeira,Bruna Gomes, Ferreira,José Luiz Pinto, Silva,Jefferson Rocha de A., Ferreira,Alexandre do Amaral, Souza,Rodrigo Octavio Mendonça Alves de, Amaral,Ana Claudia F.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Brazilian Journal of Microbiology
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822015000100261
• topic: biotransformation; monoterpene; 1,8-cineole; Mucor ramannianus; Aspergillus niger

The monoterpenoid 1,8-cineole is obtained from the leaves of Eucalyptus globulus and it has important biological activities. It is a cheap natural substrate because it is a by-product of the Eucalyptuscultivation for wood and pulp production. In this study, it was evaluated the potential of three filamentous fungi in the biotransformation of 1,8-cineole. The study was divided in two steps: first, reactions were carried out with 1,8-cineole at 1 g/L for 24 h; afterwards, reactions were carried out with substrate at 5 g/L for 5 days. The substrate was hydroxylated into 2-exo-hydroxy-1,8-cineole and 3-exo-hydroxy-1,8-cineole by fungi Mucor ramannianus and Aspergillus niger with high stereoselectivity. Trichoderma harzianum was also tested but no transformation was detected. M. ramannianus led to higher than 99% of conversion within 24 h with a starting high substrate concentration (1 g/L). When substrate was added at 5 g/L, only M. ramannianuswas able to catalyze the reaction, but the conversion level was 21.7% after 5 days. Both products have defined stereochemistry and could be used as chiral synthons. Furthermore, biological activity has been described for 3-exo-hydroxy-1,8-cineol. To the best of our knowledge, this is the first report on the use of M. ramannianus in this reaction.